Young Raymond gathered theatrical experience by performing locally during the 1950s while studying at the Royal Scottish Academy of Music and Drama (RSAMD).

He also compered the summer season pop show at the Queen's Theatre, Blackpool, starring Marty Wilde and Billy Fury.

In 1961, he got his big break on TV when he became the youngest-ever compere of Granada Television's musical quiz Spot The Tune, starring Marion Ryan.

He extended his stay in Australia after the tour ended by starring at Chequers, Sydney, and made guest appearances in the ATN-7 Channel TV series Startime before returning to Scotland.

In 1967, Raymond made a third series of Try For Ten and won the Scottish Television Personality of the Year award for his work on the show.

However, Raymond paid the price of such a heavy workload by suffering a heart attack whilst performing at the Fairfield RSL Club.

In 1980, Raymond's eighth LP, A Touch of Tartan, was released and the stage production of Scotland The Brave continued to be one of Clubland's greatest draws.

During 1981, Raymond appeared in TV and radio shows – the top-rating radio station 2CH featured him in a "Nine O'Clock Special" and he had a smash-hit season at the Manly Music Loft Theatre Restaurant with a specially devised revue, A Toast to the Tartan, which also played an eight-week season in the Sir Joseph Banks Room Theatre Restaurant at Bankstown RSL.

During 1981–84, Raymond and his company (GMA) were asked to continue producing shows for the competitive new "Club" theatre restaurant market.

Also during 1984, Raymond received a Golden Hand award by the Apex Club for his fund-raising performances for the Leukaemia Foundation at the Burdekin Theatre, North Queensland.

At the end of December 2009, Raymond resigned on amicable terms from the Gold Coast Arts Centre to concentrate on his upcoming tour of Australia in 2010.

In 2010, Raymond released a new compilation CD album, The Pride of Scotland, which is available hard copy in Australia and in downloadable format.